Preparation of vicinal N-alkylamino alcohols via acylation-rearrangement of nitrones followed by hydride reduction

RM Coates, CH Cummins

Index: Coates, Robert M.; Cummins, Clark H. Journal of Organic Chemistry, 1986 , vol. 51, # 9 p. 1383 - 1389

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Citation Number: 18

Abstract

Acylation-rearrangement of N-tert-butyl and N-cyclohexyl nitrones of cyclohexanecarboxaldehyde (l), nbutyraldehyde, isobutyraldehyde, 3- cyclbhexenecarboxaldehyde, and a-methylpropionaldehyde gave cy-pivaloyloxy imiies, which underwent reduction with lithium aluminum hydridit to N-tert-butyl-and N- cyclohexylamino alcohols (Table I). Reduction of the cy-pivaloyloxy imines derived from 1 ...